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Full text of "Practical Organic Chemistry"

244               PRACTICAL ORGANIC CHEMISTRY

metals, and derivatives of .acetamide of the following formulae
are known :

CH3CONHNa, CHa.CONHAg, (CH3.CO.NH)2I-Ig.
They are converted by nitrons acid into the organic  acid,
and in the case of substituted amides into nitrosamides,
CH3CONH2 + UNO,'         = CH,.CO.OII + N2 + H2O.

CM3.CO.NHC8H5 + HNCX = Cri.,.CO.N(NO).Q;lI5 + IIaO.

Acetanilide.                                   Nitrosoacetanilide.

With the latter class of substituted amides, PC16 forms the
imidochlorides, a reaction which is usually formulated in two
steps,

CH,.CO.NHC,H- + PC13 = CH8.CC12.NIIC,,H5 + POC1.
CII3.CCl2.NIICdII3 = CHyCCl : NCGII5 + 1IC1.

The substituted amides give both imidochloride and the
cyanide with PC15,

CII3.CONH2 + PC1S = CH3.C^QH + POC1;{ .+ IJC1.
CHs.C/'Q1"1 = CH,.CN + I LCI.

PREPARATION 13

Acetonitrile.  The various reactions by which the nitrilcs
or alkyl cyanides are obtained have already been mentioned
in one or other of the previous notes, but they may be
recapitulated.

i. By the action of KCN on the alkyl iodide or alkyl
potassium sulphate,

C.2H,I + KCN = CaIIsCN + KI.

2.   By the action of PC15 (as well as P2O5) on the amide,
CH3.CONI-L + PC15 = CH,CN + POC1, + 21IC1.
3.   By heating the aldoxime with acetic anhydride,
CH3.CH : NOII + (CH3CO)2O = CILCN + 2CIKCOOH.
They are compounds which are, for the most part, insoluble
in water, possess an ethereal smell, have a neutral reaction, ancl
may be distilled.